Social-ecological systems are breaking down at local, regional, and global scales, and sustainability seems an increasingly distant aspiration. Social harmony and economic systems are connected to ecological systems and climate, in multiple complex ways, at many scales. Adapting research practice to match integration opportunities within social-ecological systems could contribute foresight capabilities emerging from landscape change studies, which can be coupled with emerging policy transformation opportunities. The shaping of landscapes by human imagination and physical action creates meaningful contexts for building sustainability. However, the policy landscape is often dominated by circularity and “lock-in” to unsustainable pathways that are hard to escape. Moments for change emerge through timely convergence of circumstances, within a landscape context, that provide a window of opportunity—a “landscape loophole”—through which the transformation to more sustainable social-ecological relationships might be achieved. Creating future options redundancy (FOR) plans, a variety of possible pathways and alternative landscape futures within the characteristics and capacity of a region, could facilitate policy shifts and adaptive capacity, and reduce risk through reflexive future options. The convergence of circumstances providing loophole opportunities to escape existing lock-in might be understood, and even predicted, by closely coupling landscape sciences and policy research